Caulfield began his studies at the Chelsea School of Art in 1956, moving in 1960 to the Royal College of Art where he was in the class after Kitaj, Hockney and Procktor. He first showed at the Whitechapel Gallery in 1964, followed by exhibitions the at the Robert Fraser Gallery in 1965. In 1971 he began his long relationship with the Waddington Gallery. Retrospectives were held at the Walker in Liverpool and the Tate Gallery in 1981, the Serpentine, 1991 and the Hayward 1999. He became an R.A. His first painting were in oil on board but he changed over to acrylic on canvas, the paintings becoming larger and more akin to the wonderful screenprints he had been producing since 1964.
Caulfield has been a dominant figure in the world of pop-art in Britain although he bridled at being termed a pop artist. His work has influenced a generation of 'hard-edge' painters and print-makers. Although his works are figurative, with simplified shapes and areas of flat colour, his approach is almost abstract as the everyday objects he portrays are "unnaturally" juxtaposed